Diethyl Ether → tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate

HRID 1496704노트

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HRID 1496704 반응식
[Li+].[Cl-].C[Mg+].[Br-].[CH2:6](OCC)C.[O:11]=[C:12]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1.[NH4+].[Cl-]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[OH:11][C:12]1([CH3:6])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1

참가 물질

8

반응물 5

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 433294Lithium ChlorideHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 178418689HCID 178418689, 화합물

생성물 1

HCID 22951485tert-Butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate수율 83.8%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a 30 L reaction kettle was added 4 L dry THF at −10° C. After stirring, to the mixture were added ZnCl2 (118 g, 0.86 mol) and LiCl (402 g, 9.5 mol). After half an hour, to the resulting mixture was slowly added dropwisely a solution of MeMgBr (3 mol/L) in diethyl ether (6.4 L, 19.2 mol). The stirring was continued for half an hour. To the resulting mixture was slowly added a solution of tert-butyl 3-oxopyrrolidine-1-carboxylate (1600 g, 8.6 mol) in THF dropwisely. After the completion of reaction by HPLC detection, to the system was dropwisely added a saturated NH4Cl solution to quench off the reaction. The reaction was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce tert-butyl 3-hydroxy-3-methylpyrrolidine-1-carboxylate as a pale-yellow solid (1450 g) in a yield of 83.8%.

후처리

  1. customTo a 30 L reaction kettle
  2. waitAfter half an hour
  3. waitThe stirring was continued for half an hour
  4. customAfter the completion of reaction by HPLC detection
  5. customto quench off
  6. customthe reaction
  7. extractionThe reaction was extracted with ethyl acetate
  8. washThe organic phase was washed with a saturated aqueous NaCl solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. customto remove the solvent

출처 및 근거

ORD 기록
ord-14c0b46b37a14884b22474ff11b6e748
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09198902B2

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